Literature DB >> 29936708

(3+3)-Annulation of Donor-Acceptor Cyclopropanes with Diaziridines.

Alexey O Chagarovskiy1, Vladimir S Vasin1, Vladimir V Kuznetsov2, Olga A Ivanova3, Victor B Rybakov3, Alexey N Shumsky4, Nina N Makhova2, Igor V Trushkov1,5.   

Abstract

The first example of (3+3)-annulation of two different three-membered rings is reported herein. Donor-acceptor cyclopropanes in reaction with diaziridines were found to afford perhydropyridazine derivatives in high yields and diastereoselectivity under mild Lewis acid catalysis. The disclosed reaction is applicable for the broad substrate scope and exhibits an excellent functional group tolerance.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  annulation; diaziridines; donor-acceptor cyclopropanes; nitrogen heterocycles; small ring systems

Year:  2018        PMID： 29936708     DOI： 10.1002/anie.201805258

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  8 in total

1.  Lewis-Acid-Catalyzed (3+2)-Cycloadditions of Donor-Acceptor Cyclopropanes with Thioketenes.

Authors:  Grzegorz Mlostoń; Mateusz Kowalczyk; André U Augustin; Peter G Jones; Daniel B Werz
Journal:  European J Org Chem       Date:  2021-08-25

2.  Palladium-Catalyzed Cascade to Benzoxepins by Using Vinyl-Substituted Donor-Acceptor Cyclopropanes.

Authors:  Matteo Faltracco; Koen N A van de Vrande; Martijn Dijkstra; Jordy M Saya; Trevor A Hamlin; Eelco Ruijter
Journal:  Angew Chem Int Ed Engl       Date:  2021-05-26       Impact factor: 15.336

3.  Ring-Opening 1,3-Aminochalcogenation of Donor-Acceptor Cyclopropanes: A Three-Component Approach.

Authors:  André U Augustin; Peter G Jones; Daniel B Werz
Journal:  Chemistry       Date:  2019-08-07       Impact factor: 5.236

4.  Synthesis of (Het)aryl 2-(2-hydroxyaryl)cyclopropyl Ketones.

Authors:  Alexander A Fadeev; Alexey O Chagarovskiy; Anton S Makarov; Irina I Levina; Olga A Ivanova; Maxim G Uchuskin; Igor V Trushkov
Journal:  Molecules       Date:  2020-12-05       Impact factor: 4.411

5.  Enantioselective (8+3) Cycloadditions by Activation of Donor-Acceptor Cyclopropanes Employing Chiral Brønsted Base Catalysis.

Authors:  David A McLeod; Mathias Kirk Thøgersen; Casper Larsen Barløse; Mette Louise Skipper; Erlaitz Basabe Obregón; Karl Anker Jørgensen
Journal:  Angew Chem Int Ed Engl       Date:  2022-05-31       Impact factor: 16.823

6.  Total Synthesis of (+)-Cochlearol B by an Approach Based on a Catellani Reaction and Visible-Light-Enabled [2+2] Cycloaddition.

Authors:  Alistair D Richardson; Trenton R Vogel; Emily F Traficante; Kason J Glover; Corinna S Schindler
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-23       Impact factor: 16.823

Review 7.  Uncovering the Neglected Similarities of Arynes and Donor-Acceptor Cyclopropanes.

Authors:  Daniel B Werz; Akkattu T Biju
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-12       Impact factor: 15.336

8.  Selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiation.

Authors:  Alexander P Molchanov; Mariia M Efremova; Mariya A Kryukova; Mikhail A Kuznetsov
Journal:  Beilstein J Org Chem       Date:  2020-10-30       Impact factor: 2.883
  8 in total

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